


Three Times the Winchesters did Valentine's

by babybrotherdean



Category: Supernatural
Genre: Bottom Dean, Dean in Panties, Dean trying to do something nice and it going... not all that great, High Heels, Kissing, M/M, Panty Kink, Porn, Sam being a tiny child, Top Sam, Underage Kissing, Valentine's Day, Valentine's Day Fluff, Weecest, Weechesters, who loves his big brother SO MUCH
Language: English
Status: Completed
Published: 2015-03-08
Updated: 2015-03-08
Packaged: 2018-03-16 20:47:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,841
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3502274
Author URL: https://archiveofourown.org/users/babybrotherdean/pseuds/babybrotherdean
Summary: <blockquote class="userstuff">
              <p>The first time Sammy hears about Valentine’s Day, he’s five years old and it’s craft day in his kindergarten class.</p>
            </blockquote>





	Three Times the Winchesters did Valentine's

**Author's Note:**

> My piece for the [spnmonthlychalllenge's](spnmonthlychallenge.tumblr.com) February theme- Valentine's. Had a lot of fun writing this :D

The first time Sammy hears about Valentine’s Day, he’s five years old and it’s craft day in his kindergarten class. 

He’s started liking this teacher a lot. Hey name is Ms. Apico, and she’s nice to him, and she’s funny, and she doesn’t get mad when Dean comes to visit from his grade three class down the hall. When she stands up at the front of the class one day in February and starts talking about a whole day that’s dedicated to people that you love, he’s sitting up straight at attention, eyes a little bit wide with wonder.

Sammy doesn’t have a lot of people in his life. It’s never bothered him, though, not really. He’s got his dad, and he loves him a lot, but most important, he thinks, is that he’s got Dean. When Ms. Apico herds them over to the craft tables and tell them to make something for the person they love the best, there’s no doubt in his mind about what he’s going to do. 

He’s sitting by himself, mostly, for the moment. He can hear the other kids talking about making something for their moms or dads, or even for someone else in the class, but Sam’s pretty sure he’s gonna be the only one making something for his big brother. He gets glitter all over himself and glue dries into film on his fingers, but it doesn’t matter, because by the time he’s done, he knows Dean is going to love it.

-

Dean still hasn’t heard anything from his dad by the end of the school day, which means it’s still his job to pick Sammy up from kindergarten. He waves at his teacher and puts on his backpack and heads down the hall, humming cheerfully on his way to his brother’s classroom. 

Ms. Apico is there to greet him when he walks in the door, and he grins at her. She’s one of the few teachers he’s met that haven’t tried to challenge him when he’s the only one who shows up to collect Sammy at the end of the day, and he likes her for it. It’s never fun trying to explain why his dad won’t pick up the phone.

“Hi, miss,” he greets, hikes his backpack up a little higher before turning his attention towards the room as a whole. He barely has time to look around before a certain tiny, glittery kindergartener is barreling into him at full speed, and Dean laughs as he wraps his arms tight around his little brother. “Hi, Sammy.”

“Happy Val-en-tine’s,” he replies, a little muffled by Dean’s shirt. He says the word the way he always does when he’s just learned one, sounding it out carefully to make sure he gets it right. “Love you.”

Dean’s a little bit surprised by the announcement, but it’s a good surprise, like when Dad comes home early or a diner has really good apple pie. “Love you, too, Sammy. Valentine’s?” He glances up at Ms. Aprico for an explanation. He’s sort of vaguely aware of Valentine’s Day the way he’s vaguely aware of most holidays. They’re not big on celebrating, though, so he’s never really paid them much attention.

“It’s Valentine’s Day. February 14th,” she confirms, her smile partway between fond and amused. “Sam was pretty excited about it.”

“ _Love_ you,” Sammy repeats seriously, looking up at Dean with big eyes. “Love you the bestest.”

Dean smiles wide and bends down a little until he can hoist his brother up in his arms, holding him close while Sammy moves to cling to him like a koala bear. “Me, too. Didja make sometime today?”

Sammy nods intently. “It’s a surprise,” he replies. “When we get home.”

“Sounds like a plan.” Dean gives his brother a messy kiss on the cheek, then looks up at Ms. Aprico again. “Thanks, miss. Have a nice… Valentine’s.”

She grins at them and waves on their way out, Dean carrying his brother without trouble. Sam’s a small kid, and Dean kind of likes the way he can just carry him around like this.

“So… a surprise?” Dean asks, a little bit of excitement in his voice mingling with the amusement that dominates it.

“Surprise,” Sammy repeats. “I made a thing.”

Dean laughs softly, nods. “I can see that. You need a bath.”

Sammy pouts a bit, and they spend the rest of the walk just chatting idly about their days. Dean nearly forgets about the fact that it’s Valentine’s Day at all by the time he’s made a snack for them both and done his best to clean his brother up. Sammy doesn’t let him forget completely, though.

“De!” Dean’s occupied himself with sorting out the homework he’s supposed to do tonight, but he glances up at the sound of his brother’s voice. “Surprise!”

Dean comes face-to-face with a glittery, construction paper card, and he’s smiling before he can even read it properly. “Is this for me?”

“Yeah!” Sammy smiles wide and gently pushes the card into Dean’s hands before scrambling up onto the couch beside him and sprawling out in his lap. “Read it!”

Dean grins, shifts to accommodate his brother before focusing on the card again. It’s pink construction paper, folded in half, covered almost meticulously in glitter. Dean’s pretty sure he’ll be picking the stuff off of himself for weeks, but he doesn’t even care. The front says- in what he recognizes as Sammy’s slow, still-developing scrawl- _Happy Valentine’s Dean_ , and Dean has to smile again at the way _Valentine’s_ gets slightly shaky halfway through, like his brother had stopped and asked for help.

The inside, though less glittery, has more writing, several hearts drawn in red and black markers, and a picture of two people- stick figures- that Dean doesn’t have trouble recognizing, especially with the little labels underneath. _Me_ and _Dean_. 

_I love you the bestest.  
Love, Sammy._

Dean thinks he might cry, the way his heart’s swelling up, but he settles for very carefully putting down the card before wrapping his baby brother up in his arms and hugging him tight.

“I love it,” he mumbles into Sam’s hair. “Thanks, kiddo. Happy Valentine’s.”

He feels Sammy wrap skinny arms around him, just as tight. “Love you. Happy Val-en-tine’s.”

Dean smiles, presses a kiss into his brother’s hair. “Love you, too, Sammy.”

-

They don’t really celebrate Valentine’s after that. Eleven years later, though, after Dean finally kisses Sam like he’s been wanting to, and Sam doesn’t freak out like Dean had expected him to, and they’ve worked out some kind of relationship between themselves, Dean still holds onto that card, keeps it carefully tucked away along with the other little cards and trinkets that his brother has given him over the years. 

This year, though, this is different. Dean finds himself wanting to do Valentine’s for real, if only to celebrate the fact that they’re a proper couple now. It’s what results in his master plan- codename: Operation Romance- to give his little brother the best damn Valentine’s Day he’s ever had.

They’re alone- as usual- and Valentine’s, thankfully, happens to fall on a Saturday this year. Dean takes some time to gather everything he needs to see it through, and does a hell of a lot of sneaking around to do it. He thinks Sam might be suspicious, the way his brother keeps giving him amused looks, but he doesn’t care. It’ll all be worth it in the end. He’ll make sure of it.

The flowers are a pain in the ass to get- not to mention super fucking expensive- but he manages. The lady at the store assures him several times that of _course_ they’ll be okay hiding in the trunk for a while. No big deal.

There’s a lot of candy to choose from, but in the end, cinnamon hearts are on sale. They look tasty, and Dean’s all for tasty candy, so he takes them. He grabs some chocolate, too, for good measure, and hides it in the glove compartment.

The boxers end up being more of a joke than anything, but he grabs them regardless. They’ve messed around together before, more than enough for this sort of gag-gift to be acceptable. Besides, he can already imagine how good Sam’s ass is going to look in them, so he does buy them, in the end, jams them in with the candy.

His plan’s going smoothly so far. He’s on his way back to the motel to get everything set up. Sam should still be at the library, working on some partner project (and no, Dean definitely _isn’t_ jealous that Sam’s with someone else right now. On Valentine’s Day. Instead of with him, his boyfriend and big brother, and- and maybe he’s a tiny bit jealous, fine). All in all, it leaves Dean some time by himself to get everything sorted out before Sam gets back, and damn if he’s not going to make everything absolutely perfect.

Dean doesn’t realize he’s started speeding in his excitement to get back- he’s usually pretty careful about it while he’s in a small town like this- until he sees the flashing light in his rearview mirror. He swears, briefly considers trying to outrun the cop on his tail before just moving to pull over. He glances at the clock after stopping, does a quick mental calculation. Sam’s going to be home in about half an hour. He doesn’t need that much time to set up, but he still wants a few minutes to get ready, at least.

He’s already got the window rolled down by the time the cop swaggers up to his car. Dean gives him a once-over, decides he looks like a pretty typical small-town cop. Scruffy mustache, bit of a beer gut, the general air of a guy who takes himself too seriously. Dean pastes on his best charming smile as the guy leans against the frame of his car, tries to resist the urge to snap at him for probably getting his grubby fingerprints on the paintjob.

The fact that he opens with possibly the most cliché line in existence doesn’t help Dean’s impression of the guy. “D’you have any idea how fast you were goin’, son?”

Dean shrugs, figures he can play the part of the slightly-careless not-quite-teenager without much effort. “Dunno. I figure you’ll tell me, though, sir.”

The cop eyeballs him for a minute like he’s trying to decide if the response was too snarky. “Too damn fast. License and registration.”

“Yes, sir.” Dean considers it a personal victory that he doesn’t roll his eyes. He really does just want to get this over with so he can get back to the motel. He leans over to open the glove compartment, pulls out the bag on his way to get his license.

“What’s in the bag, kid?” 

Dean ignores him for a moment, finds the papers he needs and offers them to the guy. “Nothin’.” 

The cop barely glances at the papers. “Let me see it.”

For probably the tenth time during this brief encounter, Dean considers flipping the guy off and speeding away. He’s still pretty sure that’s just going to make things worse, though, so he just presses his lips together in an irritated line and grabs the bag before offering it to him.

Just as he’s watching the cop reach into the bag, just as the guy’s fingers are starting to grip the red silk of the boxers, it occurs to Dean that he’s in the Midwest, and he’s got a pair of boxers in there that he intends to give to his boyfriend, and this isn’t really the most accepting place to be, and he’s blurting out his next words before he can really think them through.

“I swear, officer, I can explain the boxers!”

That actually makes the guy stop short, and he gives Dean a strange look before pulling the offending article out. “Can you?”

“They’re a present.” Beat. “From. Uh. My girlfriend. Samantha.”

A pause. The guy looks kind of uncomfortable, which Dean tries his best not to count as a tiny victory. “Uh… right.” Another pause. He drops the boxers back in the bag and shoves it back at Dean. “Watch the speed limits next time. I’ll let you off with a warning this time, since you’re… probably in a hurry to get to. Uh. Samantha.”

Dean manages a slightly strained smile, returns the bag to the glove compartment. “Right, will do. Thanks.”

The cop tips his hat before hurrying back to his car. Dean’s back on the road before the door closes behind him. He decides not to think about the heat he can still feel high in his cheeks from that whole awkward encounter.

He’s more careful for the rest of the drive back, sticks to the speed limit even though he’s cutting it close in terms of timing. By the time he finally pulls up to the motel, he’s got maybe eight minutes before Sam gets back, which is basically no time at all, so he’s a little panicked as he starts getting everything out of the car.

Dean grabs the bag with the boxers and the other one with the candy no problem, gets out of the car and heads inside. It’s not like he’s got a whole lot to set up- it’s really just a matter of composing himself- so he sets everything down and takes the time to try to clean up a little bit. His plans for the evening are still vague, but he figures a decent-looking room is a good place to start.

Seven minutes later, he’s setting the candy on the table, eyeing it thoughtfully. The chocolate’s a no-brainer, but he’s never actually tried the candy hearts before, and he’s a little curious. 

Dean’s just popping a couple into his mouth as Sam opens that door, and his brother doesn’t even get a greeting out before he’s spitting them out, shock and disgust on his face.

“What the _fuck_ , I thought candy cinnamon hearts weren’t supposed to be spicy!”

Then Sam’s laughing, and Dean glances up and realizes his brother’s there at all, and he thinks he might be blushing. “Um. Happy Valentine’s Day?”

“Cinnamon is always spicy, Dean.” Sam rolls his eyes as he walks over, carefully avoids the rejected candies on the ground to give Dean a kiss on the cheek. “It’s like… a universal constant. Didn’t you try cinnamon gum one time?”

Dean shudders at the memory. “We don’t talk about that.” He glances towards the candy that remains before looking back at his brother. “Uh- I know it’s not a lot, but I figured I might as well try to do something, y’know? I mean, since we’re… us. Now. And shit.”

It suddenly occurs to Dean that something’s missing, and it takes him several seconds to remember the flowers he’d bought. “Wait- shit. Stay right here, okay? And don’t look in the bag!” And with that, he hurries out of the room, back towards the car. 

When he pops the trunk, all he can do for the first few seconds is stare. Because _fuck_ that lady at the store, the flowers are far from okay. They’re wilting and bruised, and when Dean very delicately picks them up, a few stray petals fall off. Not to mention that his trunk’s going to smell like roses for weeks.

He’s got a dejected sort of look when he trudges back inside, shuts the door behind him. “I promise these were nicer when I bought them,” he says quickly, half-tempted to hide the dead roses.

Sam looks confused, then almost amused as he steps forward, ducks down to smell the flowers. He straightens up a little bit, smiles. “Still smell good,” he points out. “Which is at least half of the purpose of a rose, anyways.” He pauses, then, tilts his head a little bit. “Did you plan all this for Valentine’s?”

Dean rubs at the back of his neck with his free hand. “Maybe. Kind of. Yes.” A pause. “This didn’t turn out like I planned.”

Sam laughs, takes the roses from Dean and moves to set them down on the table, pauses when he spots the extra bag there. “This part of the surprise?”

“Yeah.” Dean grins, then, because even if the shitty candy misled him and the roses aren’t exactly how they were supposed to be, at least he can maybe make Sam laugh. “Open it. They’re for you.”

Sam raises his eyebrows a little, evidently curious, and reaches into the bag. He’s laughing before he even pulls them all the way out, takes a moment to inspect them, the _sweetheart_ spelled out in black cursive on the back. “Very classy.”

“Thought you might wear them for me.” Dean steps in close again. Valentine’s surprise be damned, they’re both here, and Dean’s going to make it at least a little worthwhile. “Y’know, if you want.”

“Well…” Sam seems to consider for a moment before smiling wide. “It’s Valentine’s Day, right? Anything goes.”

Dean laughs, and they kiss, and maybe things actually turned out okay, after all.

-

Their celebrations for the next several years are few and far between. After Stanford, their relationship is rocky for a while, and with everything else to focus on- finding Dad, finding cases, all the shit that happens with the demons and the angels and Hell and everything else- it’s years before they can even think of having another proper Valentine’s.

Dean wants to do something, though. They’ve been under too much stress recently, he thinks, and Sam’s talkative when he’s drunk, and he knows there are a few fantasies his brother has that he’ll never admit to when he’s sober. Dean fully intends to bring those fantasies to life- at least for one evening.

He gets everything ready while Sam’s out at the library, checking out a possible case. After the fiasco with the cop all those years ago, Dean’s careful to give himself a massive margin for error, and makes sure he more or less sticks to the speed limit on the way home. The boxers were easy enough to explain away, but he’s pretty sure it’ll be harder this time if he gets pulled over.

He’s got an hour to get himself ready, and damn if he doesn’t take his time. Dean doesn’t consider himself an expert when it comes to this kind of shit, but he manages to get the lipstick even and smooth, bright red to accentuate what he knows are already full lips. He spends some time with the heels, too, practicing a little bit so he doesn’t break an ankle when Sam shows up. 

Since his goal for the night is sex- and hopefully lots of it- Dean decides to take the time to get himself ready. It’s always a nice surprise for Sam, and alright, yeah, maybe Dean likes the feeling of fingering himself open, likes thinking about how Sam’s going to be able to slide right in when the time comes.

The panties are last, soft and silky and far from a new thing for him. Maybe he hasn’t worn them like this since he was nineteen, and maybe Sam still doesn’t know about the Rhonda Hurley Incident, but he figures his brother will appreciate it all the same. 

After all his preparation, Dean’s left with a little time to kill before Sam gets back. He’s going full-out this year, so he takes the time to light some candles- and _fuck_ if those didn’t cost him a few games of pool- and get the room good and ready, mood lighting and all. All that’s left now is to wait, so he takes a seat on the bed, hums to himself under his breath.

Sam doesn’t take long, and Dean hears the key turning in the lock, straightens up and smiles as his brother opens the door.

It’s not hard to follow his brother’s train of thought, the way his eyes dart around the room, the way they darken when they land on Dean, the lightning-quick movement of his tongue as it wets his lips. “What’s all this?”

“Happy Valentine’s Day, Sammy.” Dean lets his smile grow, stands slowly. He’s not wobbly on the heels, thank God, and he walks towards his brother, makes sure to sway his lips a little. It’s impossible to miss the way Sam’s eyes follow the movement. “Thought we could use a bit of a break. Been too serious lately.”

Sam swallows hard, and his hands settle low on Dean’s hips as soon as he’s close enough. “You- how did…” His voice is low, rough. “How’d you know?”

“You’re an awfully talkative drunk.” Dean smiles, leans into his brother’s touch. “You like it? Been told I look pretty sexy in panties.”

Instead of responding, Sam starts walking Dean backwards, pushes him down to the bed. “Love it.” 

He makes quick work of his clothes, and Dean can’t help the grin that appears on his face when he sees the boxers Sam’s wearing.

“Those still fit?”

Sam pauses, glances down at the _sweetheart_ boxers, laughs as he seems to realize what Dean’s talking about. “They were a little big on me when you got them. I grew into them. Figured I should wear them today, if ever.”

“Guess we match, then, huh?” Dean glances down at the panties he’s wearing, red with a little black bow, then back to his brother with a smile. That seems to remind Sam of what his goal is here, and he’s quick to refocus. 

He keeps the boxers on, crawls up on the bed after Dean and situates himself between his brother’s legs. He goes for the heels, first, carefully removes each one, kisses the inside of Dean’s ankles as he does. 

“You gonna keep these?” Sam murmurs, carefully sets them on the floor next to the bed. “Because they look great on you.”

“If this is what it does to you? Fuck yes.” Dean grins, spreads his legs a little farther apart to give Sam room to settle between them. He reaches out to the bedside table, grabs the bottle on top and presents it to his brother. “C’mon, let’s get goin’.”

Sam laughs, takes the bottle and sets it aside. “Not quite yet. If you’re my present, then I’m damn well going to take the time to enjoy you properly.” He pauses, then, thoughtful, reaches out to brush his fingertips over the hem of the panties. Dean’s already hard, his erection standing out clear where it strains against the silk, a wet spot appearing where he’s leaking at the slit. “You done this before?”

Dean only hesitates a moment. “The panties? Once. Thought you might like them.”

“Love them. You’re gorgeous, Dean.” Sam ducks down, then, leans up to finally press their lips together, long and hard and deep. When he pulls away, his lips are faintly stained with the lipstick, and Dean has to grin at the sight as his brother licks it off. “Is this flavoured?”

“Yep.” Dean nods, licks his lips like he needs to prove it. “Cherry.”

That’s when Sam leans in to kiss him again, more tongue and biting and sucking than last time, and Dean isn’t afraid to moan, to arch up against him as he tries to rut against his brother.

“C’mon, Dean, gotta be patient for me,” Sam whispers against his lips. “Want to enjoy this, big brother.”

He pulls away from the kiss, then, starts working his way down Dean’s body. He takes his damn time about it, too, nips and sucks and Dean can _feel_ the bruises forming, the little love-bites that are being left littered across his skin. He’s a mess by the time Sam’s low on his stomach, nipping playfully at the skin just above the hem of the panties.

“Maybe I could fuck you while these are on,” Sam murmurs, and Dean can feel the words against his skin. “Bet you’d get them all messy, huh? Wouldn’t even be able to help yourself.”

Dean feels his cock twitch at the words, and he tries not to squirm in place. “Whatever you want,” he breathes. “M’yours.”

“I know.” Sam moves down a little farther, and then his lips are hovering over Dean’s cock, thinly veiled by the fabric of the panties, and Dean can’t even try to stop the whimper that escapes him when he feels Sam’s warm breath ghosting over his length.

“Please.” His voice is a little wrecked, and by the way Sam groans, his brother loves it.

“Yeah. Yeah, I got you,” Sam whispers, moves to mouth at Dean’s length through the panties. Dean moans, long and shameless, tries to keep his hips still. He can feel Sam’s spit soaking through the silk, and he ruts against his brother’s mouth until Sam presses his hips down against the bed.

“Soon,” he whispers. “Just- let me.” 

Dean thinks he might die if this goes on for too long, but he nods tightly, tries his best to hold still as Sam keeps going. He watches while his brother spends a little more time on his cock, then moves to kiss his way down one leg, back up the other. Dean feels like his skin’s on fire, and he’s close to begging by the time Sam’s lips brush against silk again.

“Sam- fuck, _please_. Just… need you,” he manages. “Please.”

Dean can feel the grin against his skin, and then Sam’s reaching for the lube and he thinks he might cry with relief. He spreads his legs farther apart while his brother pops the lube open.

“Just your dick,” Dean says, voice a little breathier than he’d like. “S’good. I’m good.”

Sam looks confused for a moment, but then understanding dawns, a look of wonder on his face. “You mean…?”

“Yeah.” Dean smiles, tries to ignore the fact that he’s blushing a little. “Ready and rarin’ to go.”

“You’re ridiculous.” But Sam leans down to kiss him, so Dean’s pretty sure he doesn’t care. He’s almost distracted enough to miss when his brother’s fingers slide up between his legs, when they push the panties out of the way and rub against his already-slicked up rim. He can _feel_ it when Sam moans, the way he rolls his hips to grind against the mattress.

“Fuck,” Sam mumbles, and then he’s pulling away, yanking his boxers down and off. He barely pauses long enough to slick himself up, and within seconds he’s all lined up, panties pushed aside just enough so the head of his cock is pressing against Dean’s entrance. Dean hooks his legs up around Sam’s hips, and then he’s pushing inside and _fuck_ , Dean knows he isn’t going to last very long. Judging by the look on Sam’s face, neither is he.

Sam doesn’t waste any time, moves fast and hard right from the start. They’re both a little too far-gone for coherent speech, exchanging messy kisses and barely managing to gasp out moans, each others’ names. It’s dirty, it’s desperate, and it’s everything Dean was hoping for when he got this set up.

He’s clinging to his brother, fingernails digging into the meat of Sam’s back, using the leverage to rock back hard against him. Sam’s hitting hard and deep, and Dean cries out when he feels a hit to his prostate, the way Sam shifts to focus on it on the next thrust.

It doesn’t take long after that, not with the way the silk panties are rubbing against his cock where it’s trapped between their bodies. Dean can’t even stutter out a warning before he’s coming hard, clenching tight around Sam in every way possible, and he can feel his brother so acutely, so intensely.

Dean hears a muffled _fuck_ before Sam’s lips are on his again, hard and demanding as he feels Sam finish, too. The pace slows to a dirty grind while they both ride it out, and by the time it’s over, Dean’s exhausted, still clinging to Sam, panting for breath.

Sam pulls out slowly, kisses Dean once more- softer this time- before standing up, heading to the bathroom. He’s back with a warm washcloth a moment later, and Dean stays where he is, quiet and content in the afterglow while his brother cleans them both up. Sam takes the panties off him- stained with his come, now, but he figures he can always get another pair if he has to- and manages to get him under the covers before crawling in after him.

“So… felt especially romantic today?” Sam murmurs, pulls Dean into his arms and holds him close.

Dean shrugs, curls in a little bit closer and closes his eyes. “S’like I said. We deserve a break.” He pauses, thoughtful. “I almost regret not buying the whipped cream, too.”

Sam’s silent for a moment. “You were gonna buy whipped cream?”

Dean laughs and kisses his jaw. “Maybe next year, kiddo. Happy Valentine’s Day.”

Sam laughs and hugs him closer. “Yeah. Happy Valentine’s Day, Dean.”

**Author's Note:**

> Hope you liked it, and thanks for reading!


End file.
